Summerland Key, FL Homes

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  /28

  Est $1,215,264 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft

  2237 San Remo Dr, Big Pine Key, FL 33043

  2237 San Remo Dr, Big Pine Key, FL 33043
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  /16

  $525,000

  • 1 Bed
  • 1 Bath
  • 557 Sq Ft

  31478 Avenue E, Big Pine Key, FL 33043

  ** OPEN HOUSE SAT FEB 7TH 12-2**Discover the quintessential Florida Keys lifestyle in this charming 1-bedroom, 1-bathroom island bungalow. Nestled in the heart of Big Pine Key, this home offers the perfect blend of cozy comfort and tropical serenity, making it an ideal full-time residence, weekend retreat, or savvy investment property.Home Highlights:Classic Bungalow Charm: An inviting open

  Sabre Mendoza Coldwell Banker Schmitt RE Co.

  31478 Avenue E, Big Pine Key, FL 33043
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  /54

  $1,035,000 Sold Apr 14, 2025

  29013 Marigold Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,614 Sq Ft
  • Built 1969

  Last Sold Summary

  • 13% Below List Price
  • $641/SF
  • 45 Days On Market

  Current Estimated Value $1,047,945

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  29013 Marigold Dr, Big Pine Key, FL 33043
• 

  

  /2

  Est $366,595 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,584 Sq Ft

  30869 Bay Shore Dr, Big Pine Key, FL 33043

  30869 Bay Shore Dr, Big Pine Key, FL 33043
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  /9

  $157,000

  • Land

  29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043

  ROGO EXEMPT - Buildable lot! NO wait time, build now! Incredible opportunity to buy a piece of paradise in Florida keys! This property is a unique blend of coastal living and modern amenities. Appropriate for those seeking a tranquil retreat while still being conveniently close to local attractions and the beautiful waters of the Florida Keys. Discover the lifestyle you've been dreaming of here.

  Steven Koleno Beycome of Florida, LLC

  29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043
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  /20

  $190,000 Sold Feb 27, 2025

  28587 Peg Leg Rd, Little Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 5% Below List Price
  • 80 Days On Market

  Last Listing Agent Tylon Fraley Southeast Realty Equities, Inc

  28587 Peg Leg Rd, Little Torch Key, FL 33042
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  /27

  Est $620,658 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  1537 Pandorea Ln, Big Pine Key, FL 33043

  1537 Pandorea Ln, Big Pine Key, FL 33043
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  /34

  $980,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  131 Doubloon Ln, Summerland Key, FL 33042

  3BR/2BA waterfront home on Doubloon Lane offering classic Florida Keys living and relaxation. Features include a pool, large covered patio, sun deck, and a 10,000-lb boat lift, ideal for boating and outdoor enjoyment. Upstairs living area includes impact windows and a new hot water heater (2024).The downstairs area includes two large storage rooms, one of which features a fully functioning

  Jenifer Hirsch Bluescape Real Estate

  131 Doubloon Ln, Summerland Key, FL 33042
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  /38

  $1,600,000 Sold Feb 06, 2026

  27314 Saint Lucie Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,666 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $960/SF
  • 109 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  27314 Saint Lucie Ln, Ramrod Key, FL 33042
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  /31

  Est $724,604 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  174 Newfound Blvd, Big Pine Key, FL 33043

  174 Newfound Blvd, Big Pine Key, FL 33043
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  /3

  $60,000

  • Land

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042

  Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

  Shanti Cope Coldwell Banker Schmitt Key Largo

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042
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  /3

  $65,000 Sold Aug 04, 2025

  0 Spanish Channel Dr, No Name Key, FL 33043

  • Land

  Last Sold Summary

  • 86% Below List Price
  • 54 Days On Market

  Last Listing Agent Barbara Eads Barbara Eads Realty

  0 Spanish Channel Dr, No Name Key, FL 33043
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  /64

  Est $1,640,882 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,801 Sq Ft

  553 Indies Rd, Summerland Key, FL 33042

  553 Indies Rd, Summerland Key, FL 33042
• 

  

  /5

  $139,000

  • Land

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

  Tier 3 Lot.Discover the potential of this expansive 15,000 sq ft dry lot in Sugarloaf Key, just 20 minutes from Key West, FL. Ideal for creating your dream island retreat, this property offers ample space.

  Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
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  /58

  $835,000 Sold May 28, 2025

  23920 Overseas Hwy, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 2022

  Last Sold Summary

  • 2% Below List Price
  • $672/SF
  • 60 Days On Market

  Current Estimated Value $885,254

  Last Listing Agent Aleida Ramirez United Realty Group Inc

  23920 Overseas Hwy, Summerland Key, FL 33042
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  /49

  Est $1,209,430 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  403 Indies Rd, Ramrod Key, FL 33042

  403 Indies Rd, Ramrod Key, FL 33042
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  /74

  $3,250,000

  • 4 Beds
  • 4 Baths
  • 1,804 Sq Ft

  17385 Keystone Rd, Summerland Key, FL 33042

  Stunning open water views from this fabulous waterfront home! A truly rare and highly coveted point lot on prestigious Sugarloaf Key, offering breathtaking panoramic open water views, exceptional privacy, and unmatched boating access. These point lots are extremely limited and among the most sought-after properties on Sugarloaf, prized for their expansive water frontage and commanding views of

  Lisa Swanson The Agency Florida Keys

  17385 Keystone Rd, Summerland Key, FL 33042
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  /35

  $945,000 Sold May 15, 2025

  17182 Starfish Ln W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Built 1991

  Last Sold Summary

  • 3% Below List Price
  • $747/SF
  • 6 Days On Market

  Current Estimated Value $987,943

  Last Listing Agent Daniel Urban Expert Realty LLC (HQ)

  17182 Starfish Ln W, Summerland Key, FL 33042
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  /16

  Est $919,880 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft

  273 Indies Rd, Summerland Key, FL 33042

  273 Indies Rd, Summerland Key, FL 33042
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  /21

  $875,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  27360 Saint Croix Ln, Summerland Key, FL 33042

  Enjoy the Keys lifestyle in one of the Lower Key's most desirable communities - Breezeswept! Here you'll enjoy island living with the convenience of being just a short drive to Key West. This waterfront home sits on a wide canal with 60 feet of concrete dock that includes one 15,000 boat lift, one davit set. The home is offered turnkey with all the furniture if you wish. The canal offers

  Terry Bush Bluescape Real Estate

  27360 Saint Croix Ln, Summerland Key, FL 33042
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  /32

  $825,000 Sold Apr 09, 2025

  3715 Pine St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1993

  Last Sold Summary

  • 8% Below List Price
  • $859/SF
  • 4 Days On Market

  Current Estimated Value $817,578

  Last Listing Agent Maggie Beall Lokation Real Estate

  3715 Pine St, Big Pine Key, FL 33043
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  /62

  Est $4,960,702 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,421 Sq Ft

  1141 Ocean Dr, Summerland Key, FL 33042

  1141 Ocean Dr, Summerland Key, FL 33042
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  /46

  $2,800,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  1553 Sunrise Dr, Big Pine Key, FL 33043

  Walk into this luxurious palace with captivating open water views. Light colors accenting the beautiful interior with matching large porcelain floors enhancing the large windows bringing the natural light inside. Gourmet kitchen for any chef to create great memories viewing the sunsets. Open patio with a great view of the pool and the outdoor entertaining areas. Four roomy suites for your family

  Barbara Eads Barbara Eads Realty

  1553 Sunrise Dr, Big Pine Key, FL 33043
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  /35

  $669,000 Sold Oct 24, 2025

  28212 Gato Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,077 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Below List Price
  • $621/SF
  • 80 Days On Market

  Current Estimated Value $678,865

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  28212 Gato Rd, Summerland Key, FL 33042
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  /37

  Est $1,166,166 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,368 Sq Ft

  716 Caribbean Dr E, Summerland Key, FL 33042

  716 Caribbean Dr E, Summerland Key, FL 33042
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  /51

  $837,500 Open House 3/28

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft

  29115 Rose Dr, Big Pine Key, FL 33043

  Welcome to this meticulously maintained and updated move-in ready canal-front home that offers the perfect blend of comfort, style, and durability. Featuring an inviting open-concept floor plan, this home boasts three spacious bedrooms and two modern bathrooms, all enhanced by LVP flooring throughout. Built above flood level with just the right number of steps to climb, this home ensures both

  Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  29115 Rose Dr, Big Pine Key, FL 33043
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  /41

  $650,000 Sold Jul 01, 2025

  22882 Buccaneer Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1984

  Last Sold Summary

  • 19% Below List Price
  • $580/SF
  • 81 Days On Market

  Current Estimated Value $689,014

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  22882 Buccaneer Ln, Summerland Key, FL 33042
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  /40

  Est $2,216,185 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  20995 2nd Ave W, Summerland Key, FL 33042

  20995 2nd Ave W, Summerland Key, FL 33042
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  /33

  $385,000 Under Contract

  • 1 Bed
  • 1 Bath
  • 528 Sq Ft

  30170 Linda St, Big Pine Key, FL 33043

  Welcome to your charming new home! This delightful concrete 1-bedroom, 1-bathroom residence features a sturdy metal roof and is nestled on a generously sized, fully fenced lot, offering both comfort and privacy.Step inside to discover energy-efficient LED lighting throughout, complemented by an energy-efficient A/C system to keep you cool. The kitchen features a gas range, perfect for cooking

  Silvestri Team Jeanette & Janessa Silves Coldwell Banker Schmitt Key Largo

  30170 Linda St, Big Pine Key, FL 33043
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  /28

  $598,000 Sold Feb 24, 2025

  33 E Cahill Ct, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1995

  Last Sold Summary

  • 8% Below List Price
  • $566/SF
  • 185 Days On Market

  Current Estimated Value $613,040

  Last Listing Agent Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  33 E Cahill Ct, Big Pine Key, FL 33043
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  /49

  Est $6,867,717 Not Listed For Sale

  • 10 Beds
  • 11.5 Baths
  • 10,607 Sq Ft

  17279 Oleander Ln, Sugarloaf Key, FL 33042

  17279 Oleander Ln, Sugarloaf Key, FL 33042
• 

  

  /57

  $1,595,000

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  25368 2nd St, Summerland Key, FL 33042

  Experience the perfect blend of character, durability, and Keys style at this quintessential cottage on the oceanside of Summerland Key. This thoughtfully crafted home welcomes you with the warmth of original Miami-Dade cypress floors and soaring ceilings that fill the interior with a sense of openness and timeless charm. Designed for peace of mind, the property boasts a metal roof, Hardie board

  Ally Kelley Ocean Sotheby's International

  25368 2nd St, Summerland Key, FL 33042
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  /42

  $1,450,000 Sold Jun 23, 2025

  17177 Bonita Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft
  • Built 1978

  Last Sold Summary

  • 19% Below List Price
  • $1,018/SF
  • 362 Days On Market

  Current Estimated Value $1,464,455

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  17177 Bonita Ln W, Summerland Key, FL 33042
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  /38

  Est $2,335,342 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,181 Sq Ft

  2035 Long Beach Dr, Big Pine Key, FL 33043

  2035 Long Beach Dr, Big Pine Key, FL 33043
• 

  

  /27

  $350,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042

  Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
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  /52

  $2,300,000 Sold Sep 12, 2025

  23086 Snapper Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,586 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $889/SF
  • 147 Days On Market

  Current Estimated Value $2,373,365

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  23086 Snapper Ln, Summerland Key, FL 33042
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  /30

  Est $1,003,768 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  31625 Warner St, Big Pine Key, FL 33043

  31625 Warner St, Big Pine Key, FL 33043
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  /7

  $800,000

  • Land
  • 0.18 Acre
  • $4,444,444 per Acre

  28525 Jolly Roger Dr, Little Torch Key, FL 33042

  RARE opportunity to own a build ready canal front lot in the heart of Little Torch Key. Tucked away on a quiet dead end road near the end of the island, this prime waterfront parcel offers the best of both worlds! Open water views from the front and a deep canal with seawall along the back. Enjoy unobstructed ocean and sky views from your front porch with no homes across the street ever, creating

  Fazana Haniff FHG Realty, LLC.

  28525 Jolly Roger Dr, Little Torch Key, FL 33042
• 

  

  /42

  $630,000 Sold Jul 21, 2025

  92 Frazier Ln, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 768 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $820/SF
  • 43 Days On Market

  Current Estimated Value $620,892

  Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  92 Frazier Ln, Summerland Key, FL 33042
• 

  /2

  Est $927,454 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  22974 John Avery Ln, Summerland Key, FL 33042

  22974 John Avery Ln, Summerland Key, FL 33042

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